Nathan Webb was a lawyer and a judge in Portland, Maine. He practiced family law until 1882, when he became judge of the Unites States District Court for Maine. His papers illuminate a variety of the ways in which American women's lives intersected with the legal system in the second half of the nineteenth century.

Webb was married to Jane (Jenny) Usher. Webb's papers contain the records of a controversy between two of her sisters, Martha and Elizabeth, over the estate of Elizabeth's husband, Nathaniel Osgood. The will of Nathaniel Osgood (1869) left one third of his estate to his wife Elizabeth and two thirds to his sister-in-law, Martha Usher Osgood (his brother's widow). Papers in collection deal with the settlement of the estate and the controversy over the will. In 1876, the two widows reached an agreement. The accounts of Nathaniel Osgood's estate also include the records of a disputed claim by Mary O. Cushman, who worked in Osgood's store for forty-five years.

The collection also contains the will of Martha Osgood (1889). She left her real and personal estate to her mother, sisters, and brother, to use during their lifetimes. Nathan Webb was the executor of the estate and also married to Jane Usher Webb, who stood to inherit part of Martha's estate at Rebecca's demise. Fourteen lively letters concerning the estate written in 1893 and 1894 by the fourth Usher sister, Rebecca, show a woman in firm control of her financial affairs. In 1898 the Probate Court decreed that Webb "deliver the balance of said estate to the life tenant."

Other documentation and correspondence in the Webb collection include women's wills, probate records, claims against women's estates, and investment accounts for the Usher sisters, as well as nurse and childcare payments.

The Webb collection also includes records of legal cases involving women as plaintiffs, including Annie Paine in 1872 and Emily Broad in 1875. Of particular note are two 1877 letters from schoolteacher Fannie A. Haskell concerning taking legal action against the town of New Gloucester, Maine, alleging that the town's poor maintenance of the roads caused an accident which kept her from working during the winter.